Gene cloning of an efficiency oleate hydratase from <i>Stenotrophomonas nitritireducens</i> for polyunsaturated fatty acids and its application in the conversion of plant oils to 10‐hydroxy fatty acids

Kang, Woo Ri; Seo, Min‐Ju; Shin, Kyung‐Chul; Park, Jin Byung; Oh, Deok‐Kun

doi:10.1002/bit.26058

Cited by 18 publications

(9 citation statements)

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“…Instead of using LrOhyA we used the fatty acid hydratase from Stenotrophomonas maltophilia (SmOhyA), which had been reported to exhibit a very promising specific activity of 2.7 U mg −1 (refs. 44,45 pACYC-PelBSS-OhyA) 46 was used as chassis for the recombinant expression of CvFAP (yielding a recombinant E. coli BL21 (DE3) pACYC-PelBSS-OhyA/pET28a-CvFAP). Indeed co-overexpression of both enzymes was possible ( Supplementary Fig.…”

Section: Resultsmentioning

confidence: 99%

Photobiocatalytic synthesis of chiral secondary fatty alcohols from renewable unsaturated fatty acids

et al. 2020

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En route to a bio-based chemical industry, the conversion of fatty acids into building blocks is of particular interest. Enzymatic routes, occurring under mild conditions and excelling by intrinsic selectivity, are particularly attractive. Here we report photoenzymatic cascade reactions to transform unsaturated fatty acids into enantiomerically pure secondary fatty alcohols. In a first step the C=C-double bond is stereoselectively hydrated using oleate hydratases from Lactobacillus reuteri or Stenotrophomonas maltophilia. Also, dihydroxylation mediated by the 5,8-diol synthase from Aspergillus nidulans is demonstrated. The second step comprises decarboxylation of the intermediate hydroxy acids by the photoactivated decarboxylase from Chlorella variabilis NC64A. A broad range of (poly)unsaturated fatty acids can be transformed into enantiomerically pure fatty alcohols in a simple one-pot approach.

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Section: Resultsmentioning

confidence: 99%

Photobiocatalytic synthesis of chiral secondary fatty alcohols from renewable unsaturated fatty acids

et al. 2020

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“…Partial peptide sequences of the purified OhyA from S. nitritireducens (AVNDNDPN and ITAQF) were reported previously (14). We discovered another putative fatty acid hydratase from S. maltophilia by genomic analysis based on these available partial peptide sequences.…”

Section: Resultsmentioning

confidence: 54%

“…These OhyAs showed low activity toward PUFAs. An OhyA from S. nitritireducens with high activity toward PUFAs was recently reported (14). The newly identified OhyA (OhyA2) from S. maltophilia…”

Section: Discussionmentioning

confidence: 89%

“…The biochemical properties of OhyAs from Elizabethkingia meningoseptica (6,7), Bifidobacterium breve (8,9), Streptococcus pyogenes (10), Lysinibacillus fusiformis (11), Macrococcus caseolyticus (12), Stenotrophomonas maltophilia (13), and Stenotrophomonas nitritireducens (14) have been characterized to date. All OhyAs contain flavin adenine dinucleotide (FAD)-binding motifs.…”

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confidence: 99%

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Comparison of Biochemical Properties of the Original and Newly Identified Oleate Hydratases from Stenotrophomonas maltophilia

Kang

Seo

Shin

et al. 2017

Appl Environ Microbiol

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Oleate hydratases (OhyAs) catalyze the conversion of unsaturated fatty acids to 10-hydroxy fatty acids, which are used as precursors of important industrial compounds, including lactones and -hydroxycarboxylic and ␣, -dicarboxylic acids. The genes encoding OhyA and a putative fatty acid hydratase in Stenotrophomonas maltophilia were identified by genomic analysis. The putative fatty acid hydratase was purified and identified as an oleate hydratase (OhyA2) based on its substrate specificity. The activity of OhyA2 as a holoenzyme was not affected by adding cofactors, whereas the activity of the original oleate hydratase (OhyA1) showed an increase. Thus, all characterized OhyAs were categorized as either OhyA1 or OhyA2 based on the activities of holoenzymes upon adding cofactors, which were determined by the type of the fourth conserved amino acid of flavin adenine dinucleotide (FAD)-binding motif. The hydration activities of S. maltophilia OhyA2 toward unsaturated fatty acids, including oleic acid, palmitoleic acid, linoleic acid, ␣-linolenic acid, and ␥-linolenic acid, were greater than those of OhyA1. Moreover, the specific activity of S. maltophilia OhyA2 toward unsaturated fatty acids, with the exception of ␥-linolenic acid, was the highest among all reported OhyAs. IMPORTANCE All characterized OhyAs were categorized as OhyA1s or OhyA2s based on the different properties of the reported and newly identified holo-OhyAs in S. maltophilia upon the addition of cofactors. OhyA2s showed higher activities toward polyunsaturated fatty acids (PUFAs), including linoleic acid, ␣-linolenic acid, and ␥-linolenic acid, than those of OhyA1s. This suggests that OhyA2s can be used more effectively to convert plant oils to 10-hydroxy fatty acids because plant oils contain not only oleic acid but also PUFAs. The hydration activity of the newly identified OhyA2 from S. maltophilia toward oleic acid was the highest among the activity levels reported so far. Therefore, this enzyme is an efficient biocatalyst for the conversion of plant oils to 10-hydroxy fatty acids, which can be further converted to important industrial materials. KEYWORDS Stenotrophomonas maltophilia, enzyme characterization, oleate hydrataseO leate hydratase (OhyA) converts unsaturated fatty acids to 10-hydroxy fatty acids, which are then converted to ␥-lactones by the yeasts Candida boidinii and Waltomyces lipofer (1, 2). ␥-Lactones are flavor compounds used in food and cosmetics (3). Multistep enzymatic reactions involving OhyA, alcohol dehydrogenase, Baeyer-Villiger monooxygenases, and esterase convert unsaturated fatty acids to -hydroxycarboxylic and ␣, -dicarboxylic acids (4), which are used in the preparation of resins, nylons, plastics, and lubricants (5). An effective OhyA is necessary for the efficient production of ␥-lactones, -hydroxycarboxylic acids, and ␣, -dicarboxylic acids.

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“…Kim et al used a lipase from Candida rugosa to hydrolyze olive and soybean oil, and the resulting fatty acids were then further converted by means of the Flavobacterium sp. strain DS5, which was used to oxygenate fatty acids, thus leading to 10-ketostearic acid as major product and a minor amount of 10-hydroxystearic acid when starting from olive oil [63]. Candida rugosa can also be used for the hydrolysis of safflower oil [43], as well as perilla seed oil [55,64] and tree oils [65].…”

Section: Application Of Fatty Acid Hydratase In Synthesis and Processmentioning

confidence: 99%

Fatty Acid Hydratases: Versatile Catalysts to Access Hydroxy Fatty Acids in Efficient Syntheses of Industrial Interest

Löwe

Gröger

2020

Catalysts

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The utilization of hydroxy fatty acids has gained more and more attention due to its applicability in many industrial building blocks that require it, for example, polymers or fragrances. Furthermore, hydroxy fatty acids are accessible from biorenewables, thus contributing to a more sustainable raw material basis for industrial chemicals. Therefore, a range of investigations were done on fatty acid hydratases (FAHs), since these enzymes catalyze the addition of water to an unsaturated fatty acid, thus providing an elegant route towards hydroxy-substituted fatty acids. Besides the discovery and characterization of fatty acid hydratases (FAHs), the design and optimization of syntheses with these enzymes, the implementation in elaborate cascades, and the improvement of these biocatalysts, by way of mutation in terms of the substrate scope, has been investigated. This mini-review focuses on the research done on process development using fatty acid hydratases as a catalyst. It is notable that biotransformations, running at impressive substrate loadings of up to 280 g L−1, have been realized. A further topic of this mini-review is the implementation of fatty acid hydratases in cascade reactions. In such cascades, fatty acid hydratases were, in particular, combined with alcohol dehydrogenases (ADH), Baeyer-Villiger monooxygenases (BVMO), transaminases (TA) and hydrolases, thus enabling access to a broad variety of molecules that are of industrial interest.

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Gene cloning of an efficiency oleate hydratase from Stenotrophomonas nitritireducens for polyunsaturated fatty acids and its application in the conversion of plant oils to 10‐hydroxy fatty acids

Cited by 18 publications

References 37 publications

Photobiocatalytic synthesis of chiral secondary fatty alcohols from renewable unsaturated fatty acids

Photobiocatalytic synthesis of chiral secondary fatty alcohols from renewable unsaturated fatty acids

Comparison of Biochemical Properties of the Original and Newly Identified Oleate Hydratases from Stenotrophomonas maltophilia

Fatty Acid Hydratases: Versatile Catalysts to Access Hydroxy Fatty Acids in Efficient Syntheses of Industrial Interest

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